Compound and organic light-emitting device including the same

ABSTRACT

A compound, an organic light-emitting device, and a flat display apparatus, the compound being represented by Formula 1, below:

CROSS-REFERENCE TO RELATED APPLICATION

Korean Patent Application No. 10-2014-0089799, filed on Jul. 16, 2014,in the Korean Intellectual Property Office, and entitled: “Compound andOrganic Light-Emitting Device Including The Same,” is incorporated byreference herein in its entirety.

BACKGROUND

1. Field

Embodiments relate to a compound and an organic light-emitting deviceincluding the compound.

2. Description of the Related Art

Organic light-emitting devices (OLEDs), which are self-emitting devices,may have advantages such as wide viewing angles, excellent contrast,quick response, high brightness, excellent driving voltagecharacteristics, and may provide multicolored images.

An organic light-emitting device may have a structure of a firstelectrode, a hole transport region, an emission, an electron transportregion, and a second electrode that are sequentially stacked on asubstrate. Holes injected from the first electrode may move to theemission layer via the hole transport region, and electrons injectedfrom the second electrode may move to the emission layer via theelectron transport region. Carriers, such as the holes and electrons,may recombine in the emission layer to generate excitons. When theexitons drop from an excited state to a ground state, light may beemitted.

SUMMARY

Embodiments are directed to a compound and an organic light-emittingdevice including the compound.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

According to one or more embodiments, an organic light-emitting deviceincludes a compound represented by Formula 1 below:

wherein, in Formula 1,

L is selected from a single bond, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₂-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group;

R₁ to R₅ and Ar₁ are each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇);

a, b, c, and d are each independently an integer selected from 0 to 6;

at least one substituent selected from the substituted C₁-C₆₀ alkylgroup, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynylgroup, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkylgroup, substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₂-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic condensed heteropolycyclic group isselected from,

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, carboxylic acid or a salt thereof, a sulfonic acid or asalt thereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkylgroup, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic groupand a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, carboxylic acid ora salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid ora salt thereof, C₁-C₆₀ alkyl group, C₂-C₆₀ alkenyl group, C₂-C₆₀ alkynylgroup, C₁-C₆₀ alkoxy group, C₃-C₁₀ cycloalkyl group, C₂-C₁₀heterocycloalkyl group, C₃-C₁₀ cycloalkenyl group, C₂-C₁₀heterocycloalkenyl group, C₆-C₆₀ aryl group, C₆-C₆₀ aryloxy group,C₆-C₆₀ arylthio group, C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

wherein Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ are eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₂-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

According to one or more embodiments, an organic light-emitting deviceincludes a first electrode; a second electrode facing the firstelectrode; and an organic layer that is disposed between the firstelectrode and the second electrode and includes an emission layer,wherein the organic layer includes the compound.

According to one or more embodiments, a flat display apparatus includesthe organic light-emitting device, wherein a first electrode of theorganic light-emitting device is electrically connected with a sourceelectrode or a drain electrode of a thin film transistor.

BRIEF DESCRIPTION OF THE DRAWING

Features will be apparent to those of skill in the art by describing indetail exemplary embodiments with reference to the attached drawing inwhich:

The FIGURE illustrates a schematic view of a structure of an organiclight-emitting device according to an embodiment.

DETAILED DESCRIPTION

Example embodiments will now be described more fully hereinafter withreference to the accompanying drawing; however, they may be embodied indifferent forms and should not be construed as limited to theembodiments set forth herein. Rather, these embodiments are provided sothat this disclosure will be thorough and complete, and will fullyconvey exemplary implementations to those skilled in the art.

In the drawing FIGURE, the dimensions of layers and regions may beexaggerated for clarity of illustration. Like reference numerals referto like elements throughout.

As used herein, the term “and/or” includes any and all combinations ofone or more of the associated listed items. Expressions such as “atleast one of,” when preceding a list of elements, modify the entire listof elements and do not modify the individual elements of the list.

According to an embodiment, a compound may be represented by Formula 1below:

In Formula 1,

L may be selected from a single bond, a substituted or unsubstitutedC₃-C₁₀ cycloalkylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₂-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group;

R₁ to R₅ and Ar₁ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃₋₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇).

a, b, c, and d may be each independently an integer selected from 0 to6. In an implementation, when L is a single bond, a is 1, or when a is0, a single bond may connect Ar1 to a carbon atom of the fluorene moietyof Formula 1.

At least one substituent of the substituted C₁-C₆₀ alkyl group,substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl group,substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkyl group,substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₂-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic condensed heteropolycyclic group isselected from:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkylgroup, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

wherein Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₂-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

Hereinafter, the substituents of Formula 1 will be described in detail.

According to one embodiment, in Formula 1, R₁ and R₂ may be eachindependently selected from a substituted or unsubstituted C₁-C₆₀ alkylgroup and a substituted or unsubstituted C₆-C₆₀ aryl group.

According to another embodiment, in Formula 1, R₁ and R₂ may be eachindependently a methyl group or a phenyl group.

According to another embodiment, in Formula 1, R₃ to R₅ may be eachindependently a hydrogen or a deuterium.

According to another embodiment, in Formula 1, Ar₁ may be selected froma substituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group. and asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group.

According to another embodiment, in Formula 1, Ar₁ may be a grouprepresented by one of the following Formulae 7a to 7f:

In Formulae 7a to 7f, R₃₁ to R₄₄ may be each independently selected froma hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₆-C₂₀ aryl group, a substituted or unsubstituted C₁-C₂₀heteroaryl group, a substituted or unsubstituted monovalent non-aromaticcondensed polycyclic group, and a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group;

p may be an integer selected from 1 to 4, and when p is 2 or greater,each R₃₁ may be identical to or different from each another; and

* is a binding site to a neighboring atom.

According to another embodiment, adjacent substituents or ones of theplurality of R₃₁ may be linked to each other and form a ring.

According to another embodiment, in Formula 1, a and d may be eachindependently an integer selected from 0 to 4, and a sum of a and d maybe 4.

According to another embodiment, in Formula 1, b may be 1 or 2, and cmay be an integer selected from 1 to 6.

According to another embodiment, the compound represented by Formula 1may be represented by Formula 2 below:

In Formula 2, R₁₀₁ may be selected from a hydrogen, a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a substituted or unsubstituted C₁-C₂₀alkyl group, a substituted or unsubstituted C₆-C₂₀ aryl group, asubstituted or unsubstituted C₁-C₂₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group.

According to another embodiment, the compound represented by Formula 1may be represented by Formula 3:

In Formula 3, Naph denotes a naphtyl group.

According to another embodiment, the

moiety in Formula 3 may be

In formulae of the moiety above, * denotes a binding site to aneighboring atom.

According to another embodiment, the compound represented by Formula 1may be one of Compounds 1 to 88, below.

The compound represented by Formula 1 may be synthesized by using asuitable organic synthesis method. The synthesis method may beunderstood by referring to examples described below.

The compound represented by Formula 1 may be included between a pair ofelectrodes of an OLED. In an implementation, the compound may beincluded in an emission layer (EML). Thus, provided is an OLED includinga first electrode, a second electrode facing the first electrode, and anorganic layer between the first electrode and the second electrode andincludes an EML, wherein the organic layer includes the compoundrepresented by Formula 1.

As used herein, the expression “(an organic layer) may include at leastone condensed cyclic compound” may be understood as “(an organic layer)may include one condensed cyclic compound represented by Formula 1 or atleast two different compounds selected from condensed cyclic compoundsrepresented by Formula 1”.

The organic layer may include, e.g., i) a hole transport region that isdisposed between the first electrode (an anode) and the EML and includesat least one of a hole injection layer (HIL), a hole transport layer(HTL), a buffer layer, and an electron blocking layer (EBL) and ii) anelectron transport region that is disposed between the EML and thesecond electrode (a cathode) and includes at least one of a holeblocking layer (HBL), an electron transport layer (ETL), and an electroninjection layer (EIL). For example, the EML may include the compoundrepresented by Formula 1.

As used herein, the expression “organic layer” refers to a single layerand/or multiple layers disposed between the first electrode and thesecond electrode of the OLED. However, a material included in the“organic layer” is not limited to an organic material.

The FIGURE illustrates a schematic cross-sectional view of an OLED 10according to an embodiment. The OLED 10 may include a first electrode110, an organic layer 150, and a second electrode 190.

Hereinafter, a structure of the OLED 10 and a method of manufacturingthe OLED 10 according to an embodiment will be described in detail byreferring to the FIGURE.

A substrate may be additionally disposed on a lower part of the firstelectrode 110 or an upper part of the second electrode 190 of theorganic light-emitting device 10 shown in the FIGURE. The substrate maybe a glass substrate or a transparent plastic substrate having excellentmechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water resistance.

The first electrode 110 may be formed by applying a first electrodematerial on the substrate by deposition or sputtering. When the firstelectrode 110 is an anode, the first electrode material may be selectedfrom materials having a high work function so that holes may be easilyinjected. The first electrode 110 may be a reflective electrode, asemi-transparent electrode, or a transparent electrode. Examples of thefirst electrode material may include indium-tin oxide (ITO),indium-zinc-oxide (IZO), tin oxide (SnO₂), and zinc oxide (ZnO). Also,at least one selected from magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), a Calcium (Ca), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag) may be selected as the first electrode materialto form the first electrode 110 as a semi-transparent electrode or areflective electrode.

The first electrode 110 may have a single-layered structure or amulti-layered structure including at least two layers. For example, thefirst electrode 110 may have a three-layered structure, for example,ITO/Ag/ITO, but a structure of the first electrode 110 is not limitedthereto.

The organic layer 150 is disposed on the first electrode 110. Theorganic layer 150 includes an EML.

The organic layer 150 may further include a hole transport region thatis disposed between the first electrode 110 and the EML, and/or anelectron transport region that is disposed between the EML and thesecond electrode 190.

The hole transport region may include at least one selected from an HIL,an HTL, a buffer layer, and an EBL, and the electron transport regionmay include at least one selected from an HBL, an ETL, and an EIL, butthe hole transport region and the electron transport region are notlimited thereto.

The hole transport region may have a single layer structure formed ofone material, a single layer formed of multiple different materials, ormultiple layers formed of multiple different materials.

For example, the hole transport region may have a single layer structureformed of multiple different materials or a structure of HIL/HTL,HIL/HTL/buffer layer, HIL/buffer layer, HTL/buffer layer, or HIL/HTL/EBLsequentially stacked on the first electrode 110, but a structure of thehole transport region is not limited thereto.

When the hole transport region includes an HIL, the HIL may be formed onthe first electrode 110 by using various methods such as vacuumdeposition, spin coating, casting, Langmuir-Blodgett (LB) deposition,inkjet printing, laser printing, or laser induced thermal imaging(LITI).

When the HIL is formed by vacuum deposition, the deposition conditionsmay be selected from ranges of, for example, a deposition temperature ofabout 100 to about 500° C., a degree of vacuum of about 10⁻⁸ to about10⁻³ torr, and a deposition speed of about 0.01 to about 100 Å/sec, inconsideration of a desired compound for the HIL and a desired structureof the HIL.

When the HIL is formed by spin coating, the deposition conditions may beselected from ranges of, e.g., a coating speed of about 2,000 rpm toabout 5,000 rpm and a heat treatment temperature of about 80° C. toabout 200° C. in consideration of a desired compound for the HIL and adesired structure of the HIL.

When the hole transport region includes the HTL, the HTL may be formedon the first electrode 110 or on the HIL by using various methods suchas vacuum deposition, spin coating, casting, LB deposition, inkjetprinting, laser printing, or LITI. When the HTL is formed by vacuumdeposition and spin coating, the deposition conditions and the coatingconditions of the HTL may be referred to the deposition conditions andthe coating conditions of the HIL.

The hole transport region may include at least one of m-MTDATA, TDATA,2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, α-NPB, TAPC, HMTPD,4,4′,4″-tris(N-carbazolyl)triphenylamine) (TCTA),polyaniline/Dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonicacid (Pani/CSA),polyaniline)/poly(4-styrenesulfonate (PANI/PSS), a compound representedby Formula 201, and a compound represented by Formula 202:

In Formulae 201 and 202,

descriptions of L₂₀₁ to L₂₀₅ may be each independently referred to thedescription of L of Formula 1 in the present specification;

xa1 to xa4 may be each independently an integer selected from 0, 1, 2,and 3;

xa5 may be an integer selected from 1, 2, 3, 4, and 5; and;

R₂₀₁ to R₂₀₄ may be each independently selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic heterocondensed polycyclic group.

For example, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may be each independently selected from,

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, each substituted with at least one selected from a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group;

xa1 to xa4 may be each independently an integer selected from 0, 1, and2;

xa5 may be an integer selected from 1, 2, and 3;

R₂₀₁ to R₂₀₄ may be each independently selected from,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, an azulenyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group.

The compound represented by Formula 201 may be represented by Formula201A below, but the compound is not limited thereto.

For example, the compound represented by Formula 201 may be representedby Formula 201A-1:

The compound represented by Formula 202 may be represented by Formula202A, but the compound is not limited thereto.

In Formulae 201A, 201A-1, and 202A,

descriptions of L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ may bereferred to the descriptions defined in the present specification,description of R₂₁₁ may be referred to the description of R₂₀₃, R₂₁₃ toR₂₁₆ may be each independently selected from, but are not limited to, ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticheterocondensed polycyclic group.

For example, in Formula 201A, 201A-1, and 202A,

L₂₀₁ to L₂₀₃ may be each independently selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, each substituted with at least one selected from a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group;

xa1 to xa3 may be each independently an integer selected from 0 and 1;

R₂₀₃, R₂₁₁, and R₂₁₂ may be each independently selected from,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a Spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, aphenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group;

R₂₁₃ and R₂₁₄ may be each independently selected from,

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a Spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group;

R₂₁₅ and R₂₁₆ may be each independently selected from,

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group; and

xa5 may be 1 or 2.

In an implementation, in Formulae 201A and 201A-1, R₂₁₃ and R₂₁₄ maylink to each other and form a saturated or unsaturated ring.

The compound represented by Formula 201 and the compound represented byFormula 202 may each independently include Compounds HT1 to HT20 below,but the compounds are not limited thereto:

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, e.g., about 100 Å to about 1,000 Å. When the holetransport region includes both the HIL and the HTL, a thickness of theHIL may be in a range of about 100 Å to about 10,000 Å, e.g., about 100Å to about 1,000 Å, and a thickness of the HTL may be in a range ofabout 50 Å to about 2,000 Å, e.g., about 100 Å to about 1,500 Å. Whenthicknesses of the hole transport region, the HIL, and the HTL arewithin these ranges, hole transporting properties of the organiclight-emitting device may be satisfactory without substantial increasein driving voltage.

The hole transport region may further include a charge-generatingmaterial, in addition to the materials above, to help improveconductivity. The charge-generating material may be homogenously orunhomogenously dispersed in the hole transport region.

The charge-generating material may be, e.g., a p-dopant. The p-dopantmay include one of a quinone derivative, a metal oxide, and a cyanogroup-containing compound, but the p-dopant is not limited thereto.Examples of the p-dopant may include a quinone derivative, such as atetracyanoquinonedimethane (TCNQ) and2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinondimethane (F4-TCNQ); ametal oxide, such as a tungsten oxide or a molybden oxide; and CompoundHT-D1 below, but the examples are not limited thereto:

The hole transport region may further include at least one of a bufferlayer or an EBL in addition to the HIL and the HTL. The buffer layer mayhelp increase light-emitting efficiency by compensating an opticalresonance distance according the wavelength of light emitted from theEML 13. The buffer layer may include a material that may be included inthe hole transport region. The EBL may block injection of electrons fromthe electron transport region.

The EML may be formed on the first electrode 110 or on the holetransport region by using various methods such as vacuum deposition,spin coating, casting, LB deposition, inkjet printing, laser printing,or LITI. When the EML is formed by vacuum deposition and spin coating,the deposition conditions and the coating conditions of the EML may bereferred to the deposition conditions and the coating conditions of theHIL.

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the EML may be patterned according to individualsub-pixels, such as a red EML, a green EML, and a blue EML. In animplementation, the EML may have a stacked structure of the red EML, thegreen EML, and the blue EML or a single layer structure including a redlight-emitting material, a green light-emitting material, and a bluelight-emitting material formed as a single layer and thus may emit whitelight.

The EML may include a host and a dopant.

Examples of the host may include at least one of TPBi, TBADN, ADN (alsoreferred to as “DNA”), CBP, CDBP, and TCP:

In an implementation, the host may include a compound represented byFormula 301:Ar₃₀₁-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb2)  <Formula 301>

In Formula 301,

Ar₃₀₁ may be selected from,

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene;

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic heterocondensed polycyclic group, and—Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃) (here, Q₃₀₁ to Q₃₀₃ are each independentlyselected from a hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₆-C₆₀ aryl group, and a C₂-C₆₀ heteroaryl group);

description of L₃₀₁ may be referred to the description of L₂₀₁ of thepresent specification;

R₃₀₁ may be selected from,

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group;

xb1 may be an integer selected from 0, 1, 2, and 3; and

xb2 may be an integer selected from 1, 2, 3, and 4.

For example, in Formula 301,

L₃₀₁ may be selected from,

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, and a chrysenylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, and a chrysenylene group, each substitutedwith at least one selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, anaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, and a chrysenyl group;

R₃₀₁ may be selected from,

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group,each substituted with at least one selected from a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoricacid or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group, butR₃₀₁ is not limited thereto.

For example, the host may include a compound represented by Formula301A:

In Formula 301A, descriptions of the substituents may be referred to thedescriptions in the present specification.

The compound represented by Formula 301A may include at least one ofCompounds H1 to H42, but the compound is not limited thereto:

In an implementation, the host may include at least one of Compounds H43to H49, but the host is not limited thereto:

The dopant may include a compound represented by Formula 1. In animplementation, the dopant may further include at least one of afluorescent dopant and a phosphorescent dopant, in addition to thecompound represented by Formula 1.

The phosphorescent dopant may include an organic metal complexrepresented by Formula 401:

In Formula 401,

M may be selected from iridium (Ir), platinum (Pt), osmium (Os),titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium(Tb), and thulium (Tm);

X₄₀₁ to X₄₀₄ may be each independently a nitrogen atom or a carbon atom;

rings A₄₀₁ and A₄₀₂ may be each independently selected from asubstituted or unsubstituted benzene, a substituted or unsubstitutednaphthalene, a substituted or unsubstituted fluorene, a substituted orunsubstituted spiro-fluorene, a substituted or unsubstituted indene, asubstituted or unsubstituted pyrrole, a substituted or unsubstitutedthiophene, a substituted or unsubstituted furan, a substituted orunsubstituted imidazole, a substituted or unsubstituted pyrazole, asubstituted or unsubstituted thiazole, a substituted or unsubstitutedisothiazole, a substituted or unsubstituted oxazole, a substituted orunsubstituted isooxazole, a substituted or unsubstituted pyridine, asubstituted or unsubstituted pyrazine, a substituted or unsubstitutedpyrimidine, a substituted or unsubstituted pyridazine, a substituted orunsubstituted quinoline, a substituted or unsubstituted isoquinoline, asubstituted or unsubstituted benzoquinoline, a substituted orunsubstituted quinoxaline, a substituted or unsubstituted quinazoline, asubstituted or unsubstituted carbazole, a substituted or unsubstitutedbenzoimidazole, a substituted or unsubstituted benzofuran, a substitutedor unsubstituted benzothiophene, a substituted or unsubstitutedisobenzothiophene, a substituted or unsubstituted benzooxazole, asubstituted or unsubstituted isobenzooxazole, a substituted orunsubstituted triazole, a substituted or unsubstituted oxadiazole, asubstituted or unsubstituted triazine, a substituted or unsubstituteddibenzofuran, and a substituted or unsubstituted dibenzothiophene;

at least one substituent of the substituted benzene, substitutednaphthalene, substituted fluorene, substituted spiro-fluorene,substituted indene, substituted pyrrole, substituted thiophene,substituted furan, substituted imidazole, substituted pyrazole,substituted thiazole, substituted isothiazole, substituted oxazole,substituted isooxazole, substituted pyridine, substituted pyrazine,substituted pyrimidine, substituted pyridazine, substituted quinoline,substituted isoquinoline, substituted benzoquinoline, substitutedquinoxaline, substituted quinazoline, substituted carbazole, substitutedbenzoimidazole, substituted benzofuran, substituted benzothiophene,substituted isobenzothiophene, substituted benzooxazole, substitutedisobenzooxazole, substituted triazole, substituted oxadiazole,substituted triazine, substituted dibenzofuran, and substituteddibenzothiophene may be selected from,

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₆₀ alkoxy group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticheterocondensed polycyclic group, —N(Q₄₀₁)(Q₄₀₂), —Si(Q₄₀₃)(Q₄₀₄)(Q₄₀₅),and —B(Q₄₀₆)(Q₄₀₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, and a non-aromatic condensed polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic heterocondensed polycyclic group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticheterocondensed polycyclic group, —N(Q₄₁₁)(Q₄₁₂), —Si(Q₄₁₃)(Q₄₁₄)(Q₄₁₅),and —B(Q₄₁₆)(Q₄₁₇); and —N(Q₄₂₁)(Q₄₂₂), —Si(Q₄₂₃)(Q₄₂₄)(Q₄₂₅), and—B(Q₄₂₆)(Q₄₂₇);

L₄₀₁ may be an organic ligand;

xc1 may be an integer selected from 1, 2, and 3; and

xc2 may be an integer selected from 0, 1, 2, and 3.

L₄₀₁ may be a monovalent, divalent, or trivalent organic ligand. Forexample, L₄₀₁ may be selected from a halogen ligand (e.g., Cl or F), adiketone ligand (e.g., acetylacetonate, 1,3-diphenyl-1,3-propanedionate,2,2,6,6-tetramethyl-3,5-heptanedionate, or hexafluoroacetonate), acarboxylic acid ligand (e.g., picolinate,dimethyl-3-pyrazolecarboxylate, or benzoate), a carbon monoxide ligand,an isonitrile ligand, a cyano ligand, and a phosphorus ligand (e.g.,phosphine or phosphite), but is not limited thereto.

In Formula 401, when A₄₀₁ has at least two substituents, the at leasttwo substituents of A₄₀₁ may link to each other and form a saturated orunsaturated ring.

In Formula 401, when A₄₀₂ has at least two substituents, the at leasttwo substituents of A₄₀₂ may link to each other and form a saturated orunsaturated ring.

In Formula 401, when xc1 is 2 or greater, a plurality of ligands,

may be identical to or different from each other. In Formula 401, whenxc1 is 2 or greater, A₄₀₁ and A₄₀₂ may be linked to each other bydirectly linking to another neighboring ligand of A₄₀₁ and A₄₀₂ or witha connection group (e.g., a C₁-C₅ alkylene group, —N(R′)— (here, R′ isC₁-C₁₀ alkyl group or a C₆-C₂₀ aryl group), or —C(═O)—) therebetween.

In an exemplary embodiment, the phosphorescent dopant may be selectedfrom Compounds PD1 to PD74 below, but is not limited thereto:

In an implementation, the phosphorescent dopant may include PtOEP below:

The fluorescent dopant may include at least one of DPAVBi, BDAVBi, TBPe,DCM, DCJTB, Coumarin 6, and C545T below:

In an implementation, the fluorescent dopant may include a compoundrepresented by Formula 501 below:

In Formula 501,

Ar₅₀₁ may be selected from,

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene group, a pentaphene, and anindenoanthracene;

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic heterocondensed polycyclic group, and—Si(Q₅₀₁)(Q₅₀₂)(Q₅₀₃) (here, Q₅₀₁ to Q₅₀₃ are each independentlyselected from a hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₆-C₆₀ aryl group, and a C₂-C₆₀ heteroaryl group);

descriptions of L₅₀₁ to L₅₀₃ may be each independently referred to thedescription of L₂₀₁;

R₅₀₁ and R₅₀₂ may be each independently selected from,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, anaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, and a phenyl group;

xd1 to xd3 may be each independently an integer selected from 0, 1, 2,and 3;

xb4 may be an integer selected from 1, 2, 3, and 4.

The fluorescent host may include at least one of Compounds FD1 to FD8:

An amount of the dopant in the EML may be generally within a range ofabout 0.01 part to about 15 parts by weight, based on 100 parts byweight of a host, but the amount is not limited thereto.

A thickness of the EML may be in a range of about 100 Å to about 1,000Å, e.g., about 200 Å to about 600 Å. When a thickness of the EML iswithin this range, light-emitting properties of the organiclight-emitting device may be excellent without substantial increase indriving voltage.

Next, an electron transport region may be disposed on the EML.

The electron transport region may include at least one selected from anHBL, an ETL, and an EIL, but is not limited thereto.

For example, the electron transport region may have a structure ofETL/EIL or EBL/ETL/EIL sequentially stacked on the EML, but thestructure is not limited thereto.

In an exemplary embodiment, the organic layer 150 of the organiclight-emitting device 10 may include an electron transport regiondisposed between the EML and the second electrode 190.

The electron transport region may include the HBL. When the EML includesa phosphorescent dopant, the HBL may be formed to help prevent tripletexcitons or holes from being diffused to the ETL.

When the electron transport region includes the HBL, the HBL may beformed on the EML by using various methods such as vacuum deposition,spin coating, casting, LB deposition, inkjet printing, laser printing,or LITI. When the HBL is formed by methods such as vacuum deposition andspin coating, the deposition conditions and the coating conditions ofthe HBL may be referred to the de deposition conditions and the coatingconditions of the HIL.

The HBL may include, e.g., at least one of BCP and Bphen below, but isnot limited thereto:

A thickness of the HBL may be in a range of about 20 Å to about 1,000 Å,e.g., about 30 Å to about 300 Å. When a thickness of the HBL is withinthis range, hole blocking properties of the organic light-emittingdevice may be excellent without substantial increase in driving voltage.

The electron transport region may include the ETL. The ETL may be formedon the EML or the HBL by using various methods such as vacuumdeposition, spin coating, casting, LB deposition, inkjet printing, laserprinting, or LITI. When the ETL is formed by methods such as vacuumdeposition and spin coating, the deposition conditions and the coatingconditions of the ETL may be referred to the de deposition conditionsand the coating conditions of the HIL.

In an exemplary embodiment, the organic layer 150 of the organiclight-emitting device 10 may include an electron transport regionbetween the EML and the second electrode 190. The electron transportregion may include the ETL.

The ETL may include at least one selected from BCP and Bphen above andAlq_(a), Balq, TAZ, and NTAZ below:

A thickness of the ETL may be in a range of about 100 Å to about 1,000Å, e.g., about 150 Å to about 500 Å. When a thickness of the ETL iswithin this range, electron transporting properties of the organiclight-emitting device may be excellent without substantial increase indriving voltage.

The ETL may further include a metal-containing material in addition tothe materials above.

The metal-containing material may include a Li-complex. The Li-complexmay include, for example, compound ET-D1 (lithium quinolate (LiQ)) orET-D2:

The electron transport region may include the EIL that facilitatesinjection of electrons from the second electrode 190.

The EIL may be formed on the ETL by using various methods such as vacuumdeposition, spin coating, casting, LB deposition, inkjet printing, laserprinting, or LITI. When the EIL is formed by vacuum deposition and spincoating, the deposition conditions and the coating conditions of the EILmay be referred to the de deposition conditions and the coatingconditions of the HIL.

The EIL may include at least one selected from LiF, NaCl, CsF, Li₂O,BaO, and LiQ.

A thickness of the EIL may be in a range of about 1 Å to about 100 Å,e.g., about 3 Å to about 90 Å. When a thickness of the EIL is withinthis range, electron injecting properties of the organic light-emittingdevice may be excellent without substantial increase in driving voltage.

The second electrode 190 may be disposed on the organic layer 150. Thesecond electrode 190 may be a cathode, which is an electron injectionelectrode. In this regard, a material for forming the second electrode190 may include a metal, an alloy, an electric conducting compound, anda mixture thereof having a low work function. For example, the secondelectrode 190 may be a thin film formed of lithium (Li), magnesium (Mg),aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium(Mg—In), or magnesium-silver (Mg—Ag). Also, ITO or IZO may be used as amaterial for forming the second electrode 190. The second electrode 190may be a reflective electrode, a semitransparent electrode, or atransparent electrode.

In an implementation, an organic layer of an organic light-emittingdevice according to an embodiment may be formed by using a depositionmethod using a compound according to an embodiment or by using a wetmethod, in which the organic light-emitting device is coated with thecompound that is prepared as a solution.

An organic light-emitting device according to an embodiment may beincluded in various types of flat panel displays, e.g., a passive matrixorganic light-emitting display apparatus and an active matrix organiclight-emitting display apparatus. For example, when the organiclight-emitting device is included in an active matrix organiclight-emitting display apparatus, a first electrode located on a side ofa substrate is a pixel electrode which may be electrically connected toa source electrode or a drain electrode of a thin film transistor. In animplementation, the organic light-emitting device may be included in aflat panel display that may display images on both surfaces.

The organic light-emitting device has been described with reference tothe FIGURE, but an organic light-emitting device is not limited thereto.

Hereinafter, representative substituents among the substituents in thepresent specification are defined as follows (the number of carbonsdefining a substituent is not limited and does not particularly limitcharacteristics of the substituent, and definition of a substituent notdefined in the present specification follows general definitionthereof).

As used herein, a C₁-C₆₀ alkyl group denotes a monovalent linear orbranched aliphatic hydrocarbon group, and examples of the C₁-C₆₀ alkylgroup include a methyl group, an ethyl group, a propyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group,an iso-amyl group, and a hexyl group. As used herein, examples of aC₁-C₆₀ alkylene group include a divalent group that has the samestructure as the C₁-C₆₀ alkyl group.

As used herein, a C₁-C₆₀ alkoxy group denotes a monovalent group havinga formula of —OA₁₀₁ (here, A₁₀₁ is the C₁-C₆₀ alkyl group), and examplesof the C₁-C₆₀ alkoxy group include a methoxy group, an ethoxy group, andan isopropyloxy group.

As used herein, a C₂-C₆₀ alkenyl group has a structure including atleast one carbon-carbon double bond in the middle or at an end of theC₂-C₆₀ alkyl group, and examples of the C₂-C₆₀ alkenyl group include anethenyl group, a propenyl group, and a butenyl group. As used herein, aC₂-C₆₀ alkenylene group denotes a divalent group that has the samestructure as the C₂-C₆₀ alkenyl group.

As used herein, a C₂-C₆₀ alkynyl group has a structure including atleast one carbon-carbon triple bond in the middle or at an end of theC₂-C₆₀ alkyl group, and examples of the C₂-C₆₀ alkynyl group include anethynyl group and a propynyl group. As used herein, a C₂-C₆₀ alkynylenegroup denotes a divalent group that has the same structure as the C₂-C₆₀alkynyl group.

As used herein, a C₃-C₁₀ cycloalkyl group denotes a C₃-C₁₀ monovalentsaturated hydrocarbon monocyclic group, and examples of the C₃-C₁₀cycloalkyl group include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, and a cycloheptyl group. As usedherein, a C₃-C₁₀ cycloalkylene group denotes a divalent group that hasthe same structure as the C₃-C₁₀ cycloalkyl group.

As used herein, the C₂-C₁₀ heterocycloalkyl group denotes a C₂-C₁₀monovalent monocyclic group including at least one hetero atom selectedfrom N, O, P, and S as a ring-forming atom, and examples of the C₂-C₁₀heterocycloalkyl group include a tetrahydrofuranyl group and atetrahydrothiophenyl group. As used herein, a C₂-C₁₀ heterocycloalkylenegroup denotes a divalent group that has the same structure as the C₂-C₁₀heterocycloalkyl group.

As used herein, a C₃-C₁₀ cycloalkenyl group denotes a C₃-C₁₀ monovalentmonocyclic group having at least one double bond in the ring while notlosing its aromacity, and examples of the C₃-C₁₀ cycloalkenyl groupinclude a cyclopentyl group, a cyclohexenyl group, and a cycloheptenylgroup. As used herein, the C₃-C₁₀ cycloalkenylene group denotes adivalent group that has the same structure as the C₃-C₁₀ cycloalkenylgroup.

As used herein, a C₂-C₁₀ heterocycloalkenyl group denotes a C₂-C₁₀monovalent monocyclic group including at least one hetero atom selectedfrom N, O, P, and S as a ring-forming atom and at least one double bondin the ring, and examples of the C₂-C₁₀ heterocycloalkenyl group includea 2,3-hydrofuranyl group and a 2,3-hydrothiophenyl group. As usedherein, a C₂-C₁₀ heterocycloalkenylene group denotes a divalent groupthat has the same structure as the C₂-C₁₀ heterocycloalkenyl group.

As used herein, a C₆-C₆₀ aryl group denotes a monovalent group having aC₆-C₆₀ carbocyclic aromatic system, and a C₆-C₆₀ arylene group denotes adivalent group that has a C₆-C₆₀ carbocyclic aromatic system. Examplesof the C₆-C₆₀ aryl group include a phenyl group, a naphthyl group, ananthracenyl group, a phenanthrenyl group, a pyrenyl group, and achrysenyl group. As used herein, when the C₆-C₆₀ aryl group and theC₆-C₆₀ arylene group include at least two rings, the rings may be fusedto each other.

As used herein, a C₂-C₆₀ heteroaryl group denotes a monovalent groupincluding at least one heteroatom selected from N, O, P, and S as aring-forming atom and having a C₂-C₆₀ carbocyclic aromatic system, and aC₁-C₆₀ heteroarylene group denotes a divalent group including at leastone heteroatom selected from N, O, P, and S as a ring-forming atom andhaving a C₂-C₆₀ carbocyclic aromatic system. Examples of the C₁-C₆₀heteroaryl group include a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group. When the C₂-C₆₀ heteroaryl group anda C₂-C₆₀ heteroarylene group include at least two rings, the rings maybe fused to each other.

As used herein, a C₆-C₆₀ aryloxy group denotes —OA₁₀₂ (here, A₁₀₂ is theC₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group denotes —SA₁₀₃ (here,A₁₀₃ is the C₆-C₆₀ aryl group).

As used herein, a monovalent non-aromatic condensed polycyclic groupdenotes a monovalent group having at least two rings that are condensedto each other, including only carbon as a ring-forming atom (e.g., thenumber of the included carbon atoms may be 8 to 60), and havingnon-aromaticity, as a whole molecule. Examples of the non-aromaticcondensed polycyclic group include a fluorenyl group. As used herein, adivalent non-aromatic condensed polycyclic group denotes a divalentgroup that has the same structure as the monovalent non-aromaticcondensed polycyclic group.

As used herein, a monovalent non-aromatic heterocondensed polycyclicgroup denotes a monovalent group having at least two rings that arecondensed to each other, including a heteroatom selected from N, O, P,and S in addition to carbon as a ring-forming atom (e.g., the number ofthe included carbon atoms included may be 2 to 60), and havingnon-aromacity as a whole molecule. Examples of the non-aromaticheterocondensed polycyclic group include a carbazolyl group. As usedherein, a divalent non-aromatic heterocondensed polycyclic group denotesa divalent group that has the same structure as the monovalentnon-aromatic heterocondensed polycyclic group.

As used herein, at least one substituent of the substituted C₃-C₁₀cycloalkylene group, substituted C₂-C₁₀ heterocycloalkylene group,substituted C₃-C₁₀ cycloalkenylene group, substituted C₂-C₁₀heterocycloalkenylene group, substituted C₆-C₆₀ arylene group,substituted C₂-C₆₀ heteroarylene group, substituted divalentnon-aromatic condensed polycyclic group, substituted divalentnon-aromatic heterocondensed polycyclic group, substituted C₁-C₆₀ alkylgroup, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynylgroup, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkylgroup, substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₂-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic heterocondensed polycyclic group isselected from,

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkylgroup, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy,a C₆-C₆₀ arylthio, a C₂-C₆₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, a monovalent non-aromatic heterocondensedpolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy, a C₆-C₆₀ arylthio, a C₂-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic heterocondensed polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy, a C₆-C₆₀ arylthio, a C₂-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic heterocondensed polycyclic group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy, a C₆-C₆₀ arylthio, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic heterocondensed polycyclic group, N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ are, eachindependently, selected from a hydrogen, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₂-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic heterocondensed polycyclic group.

For example, at least one substituent of the substituted C₃-C₁₀cycloalkylene group, substituted C₂-C₁₀ heterocycloalkylene group,substituted C₃-C₁₀ cycloalkenylene group, substituted C₂-C₁₀heterocycloalkenylene group, substituted C₆-C₆₀ arylene group,substituted C₂-C₆₀ heteroarylene group, substituted divalentnon-aromatic condensed polycyclic group, substituted divalentnon-aromatic heterocondensed polycyclic group, substituted C₁-C₆₀ alkylgroup, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynylgroup, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkylgroup, substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₂-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic heterocondensed polycyclic group isselected from,

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a cyclopentylgroup, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acycloheptenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coroneryl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, —N(Q₁₁)(Q₁₂),—Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇);

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cycloheptenyl group, a cyclohexenyl group, aphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coroneryl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, an indolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzooxazolylgroup, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a thiadiazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cycloheptenyl group, a cyclohexenyl group, aphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coroneryl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, an indolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzooxazolylgroup, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a thiadiazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cycloheptenyl group, a cyclohexenyl group, aphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coroneryl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, an indolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzooxazolylgroup, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a thiadiazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ are, eachindependently, selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acycloheptenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coroneryl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group.

The term “Ph” used herein refers to a phenyl group, the term “Me” usedherein refers to a methyl group, the term “Et” used herein refers to anethyl group, and the term “ter-Bu” or “But” used herein refers to atert-butyl group.

Hereinafter, an OLED according to an embodiment will now be described inmore detail with reference to the following examples. In the examples,the expression “B was used instead of A” indicates that an amount permol of A and an amount per mol of B are the same.

The following Examples and Comparative Examples are provided in order tohighlight characteristics of one or more embodiments, but it will beunderstood that the Examples and Comparative Examples are not to beconstrued as limiting the scope of the embodiments, nor are theComparative Examples to be construed as being outside the scope of theembodiments. Further, it will be understood that the embodiments are notlimited to the particular details described in the Examples andComparative Examples.

SYNTHESIS EXAMPLE Synthesis Example 1: Synthesis of Compound 23Synthesis of Compound 23-1

10 g of 2-bromobenzyl bromide (40 mmol) and 12.58 g oftriphenylphosphine (48 mmol) were mixed with 500 ml of toluene, asolvent, to prepare a solution, and then the solution was heated andstirred for 3 hours. When the reaction was completed, the solution wascooled to room or ambient temperature, and then its precipitate wasfiltered by using hexane to obtain 19.6 g of Compound 23-1((2-bromobenzyl) triphenyl phosphonium bromide) as a white solid (yield:96.1%).

1H NMR (300 MHz, CDCl3): δ (ppm) 7.8˜37.21 (m, 16H), 7.38 (d, J=7.8 Hz,1H), 7.17 (m, 2H), 5.74 (d, J=14.4 Hz, 2H)

Molecular weight: 431.0559 (theoretical value of C25H21BrP+)

LR-Mass (EI+): 431.0, HR-Mass (FAB+): 431.0564

Synthesis of Compound 23-2

10 g of 2-iodobenzylalcohol (42.73 mmol) was mixed with 200 mL ofdichloromethane to prepare a solution, 10.13 g of pyridiumchlorochromate (47 mmol) was added thereto, and the solution was stirredat ambient temperature. When the reaction was completed, the solvent wasremoved, and the resultant was purified by using a column chromatography(eluent, ethyl acetate:hexane=1:8) to obtain 9.1 g of Compound 23-2(2-iodobenzaldehyde) as a yellow liquid (yield: 92%).

1H NMR (300 MHz, CDCl3): δ (ppm) 10.09 (s, 1H), 7.94 (dd, J=15.0, 7.2Hz, 2H), 7.48 (s, 1H), 7.30 (s, 1H)

Molecular weight: 231.9385 (theoretical value of C7H5IO)

LR-Mass (EI+): 232.0, HR-Mass (EI+): 231.9393

Synthesis of Compound 23-3

33 g of Compound 23-1 (2-bromobenzyl)triphenylphosphonium bromide)(64.425 mmol) and 350 mL of tetrahydrofuran were stirred under anitrogen atmosphere at a temperature of 0° C. Then, a mixture preparedby mixing 8.434 g of potassium tert-butoxide (75.163 mmol) and 50 mL oftetrahydrofuran was added thereto, a mixture of 12.457 g of Compound23-2 (2-iodobenzaldehyde) (53.688 mmol) and 100 mL of tetrahydrofuranwas dropwisely added thereto, a temperature of the solution was slowlychanged to ambient temperature, and the solution was stirred for 24hours. When the reaction was completed, 100 mL of H₂O was added,stirred, and then an organic layer was separated therefrom by using alarge amount of diethyl ether and H₂O. Then, the resultant was washedwith a saturated sodium chloride solution, and sodium sulfate was usedto remove water therefrom. The solvent was removed from the resultantthus obtained, and column chromatography was performed under a hexanecondition to obtain 18.7 g of Compound 23-3((Z)-1-bromo-2-(2-iodostyryl)benzene) as a white solid (yield: 90.5%).

1H NMR (300 MHz, CDCl3): δ (ppm) 7.87 (dd, J=7.9, 1.1 Hz, 1H), 7.57 (dd,J=7.3, 1.8 Hz, 1H), 7.11-6.93 (m, 5H), 6.89 (td, J=7.7, 1.9 Hz, 1H),6.76 (d, J=11.8 Hz, 1H), 6.68 (d, J=11.8 Hz, 1H)

13C NMR (75 MHz, CDCl3): δ (ppm) 140.9, 139.2, 137.0, 135.4, 132.8,131.1, 130.8, 130.6, 129.0, 128.9, 128.0, 127.1, 124.3, 100.0

Molecular weight: 383.9011 (theoretical value of C14H10BrI)

LR-Mass (EI+): 384.1, HR-Mass (EI+): 383.9018

Synthesis of Compound 23-4

15.1 g of Compound 23-3 (39.217 mmol), 13.697 g of tributyltin hydride(47.060 mmol), and 1.288 g of azobisisobutyronitrile (AIBN) (7.843 mmol)were added to 200 mL of toluene, and the mixture was heated and stirredunder a nitrogen atmosphere. After 12 hours, the mixture was slowlycooled to ambient temperature, and then 2.283 g of tributyltin hydride(7.843 mmol) and 0.258 g of AIBN (1.569 mmol) were added thereto, andthe solution was heated and stirred. When the reaction was completed,toluene was removed from the resultant, and an organic layer wasseparated by using a large amount of dichloromethane and H₂O, a tin saltwas removed by using potassium fluoride and Celite, washed with asaturated sodium chloride solution, and sodium sulfate was used toremove water therefrom. The solvent was removed from the resultant thusobtained, and column chromatography was performed under a hexanecondition to obtain 8.4 g of Compound 23-4 (1-bromophenanthrene) as awhite solid (yield: 83.3%).

1H NMR (300 MHz, CDCl3): δ (ppm) 8.68 (d, J=8.2 Hz, 2H), 8.23 (d, J=9.2Hz, 1H), 7.95˜6.89 (m, 2H), 7.86 (d, J=9.2 Hz, 1H), 7.73˜7.62 (m, 2H),7.50 (dd, J=8.2, 7.9 Hz, 1H)

13C NMR (75 MHz, CDCl3): δ (ppm) 132.2, 132.1, 130.9, 130.8, 130.1,128.9, 128.7, 127.4, 127.3, 127.0, 125.5, 123.9, 123.1, 122.5

Molecular weight: 255.9888 (theoretical value of C14H9Br)

LR-Mass (EI+): 256.0, HR-Mass (EI+): 255.9886

Synthesis of Compound 23-5

3 g of Intermediate 23-4 (11.667 mmol) was added to a 2-neck roundbottom flask, sealed, and dried at a low pressure. 100 mL of purifiedtetrahydrofuran was added thereto, and a temperature was maintained at−78° C. by using dry ice and acetone. 11.667 mL of n-butyl lithiumsolution (2.5 mol/L in hexane) (29.168 mmol) was slowly injected theretoand stirred for 1 hour while the temperature was maintained, 6.539 mL oftrimethylborate (58.336 mmol) was added, and then the solution wasstirred while its temperature was slowly changed to ambient temperature.After 5 hours, a large amount (20 mL) of 1N HCl was added thereto, andthe solution was stirred for 2 hours. When the reaction was completed,an organic layer was separated by using a large amount (e.g., excess) ofdichloromethane and H₂O, and sodium sulfate was used to remove watertherefrom. The solvent was removed from the resultant thus obtained, andcolumn chromatography (eluent, dichloromethane:methanol=9:1) wasperformed to obtain 1.8 g of Compound 23-5 (phenanthren-1-ylboronicacid) as a white solid (yield: 69.5%).

1H NMR (300 MHz, acetone-d6): δ (ppm) 8.88 (dd, J=8.4, 5.4 Hz, 2H), 8.51(d, J=9.0 Hz, 1H), 7.97 (d, J=7.2 Hz, 2H), 7.82 (d, J=9.0 Hz, 1H),7.71˜7.60 (m, 3H)

13C NMR (75 MHz, acetone-d6): δ (ppm) 135.0, 132.8, 131.8, 130.6, 128.3,127.7, 126.5, 126.4, 126.3, 125.7, 124.0, 122.7

Molecular weight: 222.0852 (theoretical value of C14H11BO2)

LR-Mass (EI+): 222.0, HR-Mass (EI+): 222.0848

Synthesis of Compound 23-6

3.849 g of methyl 5-bromo-2-iodobenzoate (11.259 mmol), 3 g of Compound23-5 (phenanthren-1-ylboronic acid) (13.510 mmol), 2 mol/L potassiumcarbonate (in H₂O, 30 mL), and 0.651 g oftetrakis(triphenylphosphine)palladium (0.563 mmol) were mixed with 100mL of tetrahydrofuran and 30 mL of methanol under a nitrogen atmosphere,and the solution was heated and stirred. After 24 hours, completion ofthe reaction was confirmed by TLC, and the solvent was removedtherefrom, filtered by using Celite. Then, an organic layer wasseparated, washed with a saturated sodium chloride solution, and sodiumsulfate was used to remove water therefrom. The solvent was removed fromthe resultant thus obtained, and column chromatography (eluent,MC:hexane=1:4) was performed to obtain 3.5 g of Compound 23-6(1-bromophenanthrene) as a white solid (yield: 79%).

1H NMR (300 MHz, CDCl3): δ (ppm) 8.80 (d, J=12.6 Hz, 2H), 8.22 (s, 1H),7.88 (d, J=7.8 Hz, 1H), 7.77 (dd, J=5.1, 1.8 Hz, 1H), 7.73˜7.60 (m, 4H),7.40 (dd, J=7.8, 1.5 Hz, 2H), 7.32 (d, J=8.1 Hz, 1H), 3.41 (s, 3H)

13C NMR (75 MHz, CDCl3): δ (ppm) 166.4, 140.7, 139.0, 134.6, 133.5,133.1, 131.7, 130.3, 130.2, 130.0, 128.5, 127.2, 126.8, 126.7, 125.7,123.9, 122.9, 122.4, 121.5, 52.1

Molecular weight: 390.0255 (theoretical value of C22H15BrO2)

LR-Mass (EI+): 392.2, HR-Mass (EI+): 392.0257

Synthesis of Compound 23-7

3.45 g of Compound 23-6 (methyl 5-bromo-2-(phenanthren-1-yl)benzoate)(8.818 mmol) was added to a 2-neck round bottom flask, sealed, and thendried at a low pressure. 120 mL of purified tetrahydrofuran was addedthereto, 14.85 mL of methyl magnesium bromide solution (1.4 mol/L,21.162 mmol) was slowly injected, and the solution was heated andstirred for 4 hours. Then, the solvent was removed, an organic layer wasseparated by using a large amount of dichloromethane and H₂O, washedwith a saturated sodium chloride solution, and sodium sulfate was usedto remove water therefrom. The solvent was removed from the resultantthus obtained, and column chromatography (eluent, MC:hexane=1:9) wasperformed to obtain 2.7 g of Compound 23-7(2-(5-bromo-2-(phenanthren-1-yl)phenyl)propan-2-ol) as a white solid(yield: 75%).

1H NMR (300 MHz, CDCl3): δ (ppm) 8.77 (d, J=5.1 Hz, 2H), 8.03 (d, J=1.8Hz, 1H), 7.89 (d, J=4.5 Hz, 1H), 7.88˜7.62 (m, 4H), 7.52˜7.47 (m, 2H),7.33 (d, J=9.3 Hz, 2H), 7.03 (d, J=8.1 Hz, 1H), 1.39 (s, 3H), 1.22 (s,3H)

13C NMR (75 MHz, CDCl3): δ (ppm) 149.5, 140.4, 1367, 134.2, 131.7,131.0, 130.5, 130.2, 129.6, 129.4, 128.6, 128.0, 127.2, 126.9, 125.4,125.0, 122.9, 122.5, 122.1, 73.7, 32.3, 31.7

Molecular weight: 390.0619 (theoretical value of C23H19BrO)

LR-Mass (EI+): 390.0, HR-Mass (EI+): 390.0622

Synthesis of Compound 23-8

4.5 mL of sulfuric acid was added to 2.7 g of Compound 23-7(2-(5-bromo-2-(phenanthren-1-yl)phenyl)propan-2-ol) (6.918 mmol) in 130mL of acetic acid, a solvent, and the solution was heated and stirredfor 3 hours. After the reaction was completed, a temperature of thesolution was slowly changed to ambient temperature, 50 mL of H₂O wasadded thereto, and stirred. An organic layer was separated by usingdichloromethane and H₂O, washed with a saturated sodium chloridesolution, and sodium sulfate was used to remove water therefrom. Thesolvent was removed from the resultant thus obtained, and columnchromatography was performed under a hexane condition to obtain 2.7 g ofCompound 23-8 (9-bromo-7,7-dimethyl-7H-indeno[1,2-a]phenanthrene) as awhite solid (yield: 75%).

1H NMR (300 MHz, CDCl3): δ (ppm) 8.76 (t, J=5.4 Hz, 2H), 8.63 (d, J=9.3Hz, 1H), 8.24 (d, J=8.4 Hz, 1H), 7.74 (d, J=8.7 Hz, 1H), 7.9˜77.91 (m,2H), 7.7˜7.59 (m, 4H), 1.59 (s, 6H)

13C NMR (75 MHz, CDCl3): δ (ppm) 157.0, 152.7, 130.2, 128.6, 127.9,126.9, 126.7, 126.5, 126.2, 124.7, 123.0, 122.3, 120.9, 120.7, 46.6,26.9

Molecular weight: 372.0514 (theoretical value of C23H17Br)

LR-Mass (EI+): 372.0, HR-Mass (EI+): 372.0514

Synthesis of Compound 23-9

50 g of 1-naphthylhydrazine (316.30 mmol) and 170 ml of acetic acid wereadded to a 500 ml round bottom flask and heated, so that a temperatureof the solution was 60° C. 35.45 g of 2-methylcyclohexanone (316.30mmol) was dropwisely added to the heated solution in the flask. When theaddition was completed, the solution was refluxed for 8 hours. Aftercompleting the reaction, 100 ml of water was added thereto, and thesolution was basified by using sodium hydroxide. An organic layer wasextracted with water and ethyl acetate, water was removed with magnesiumsulfate, concentrated at a low pressure, and purified by using columnchromatography by using hexane and ethyl acetate as an eluent to obtain62.47 g of Compound 23-9 (265.69 mmol) (yield: 84%).

Synthesis of Compound 23-10

50 g of Compound 23-9 (212.64 mmol) was dissolved in 570 mL of toluenein a 2-neck round bottom flask in a nitrogen atmosphere, and atemperature of the solution was decreased to −10° C. 202 ml of 1.6 Mmethyllithium (318.96 mmol) was slowly and dropwisely added to thesolution in the flask, and allowed to react for 3 hours at −10° C. Whenthe reaction was completed, water was slowly added until reactivity wasundetecable. An organic layer was extracted with water and ethylacetate, water was removed with magnesium sulfate, and concentrated at alow pressure. The resultant was then purified by using columnchromatography by using hexane and ethylacetate as an eluent to obtain40.59 g of Compound 23-10 (161.61 mmol) (yield: 76%).

Synthesis of Compound 23

10 g of Compound 23-8 (26.88 mmol), 8.77 g of Compound 23-10 (34.95mmol), 0.15 g of palladium acetate (Pd(OAc)₂) (0.54 mmol), 5.22 g ofsodium tert-butoxide (53.76 mmol), 0.11 g of tritert-butyl phosphine(0.54 mmol), and 100 ml of toluene were added to a round bottom flaskand reacted at a reaction temperature of 100° C. for 2 hours. When thereaction was completed, the solution was filtered, the filtered solutionwas concentrated, and then purified by using a column chromatography.The produced solid was recrystallized with toluene and methanol,filtered, and dried to obtain 9.49 g of Compound 23 (17.47 mmol, yield:65%).

MS: m/z 543 [M]+

Synthesis Example 2: Synthesis of Compound 25

9.93 g (18.28 mmol) of Compound 25 (yield: 68%) was obtained in the samemanner as in the synthesis of Compound 23 of Synthesis Example 1, exceptthat 2-naphthylhydrazine was used instead of 1-naphthylhydrazine.

MS: m/z 543 [M]+

Synthesis Example 3: Synthesis of Compound 33 Synthesis of Compound 33-1

50 g of phenylhydrazine (462 mmol) and 170 ml of acetic acid were addedto a 500 ml round bottom flask and heated, so that a temperature of thesolution was 60° C. 51.9 g of 2-methylcyclohexanone (462 mmol) wasdropwisely added to the heated solution in the flask. When the additionwas completed, the solution was refluxed for 8 hours. After completingthe reaction, 100 ml of water was added thereto, and the solution wasbasified by using sodium hydroxide. An organic layer was extracted withwater and ethylacetate, water was removed with magnesium sulfate,concentrated at a low pressure, and purified by using columnchromatography by using hexane and ethyl acetate as an eluent to obtain72 g of Compound 33-1 (388.08 mmol) (yield: 84%).

Synthesis of Compound 33-2

57 g of Compound 33-1 (308 mmol) was dissolved in 570 mL of toluene in a2 L round bottom flask under a nitrogen atmosphere, and a temperature ofthe solution was decreased to −10° C. 300 ml of 1.6 M methyllithium (474mmol) was slowly and dropwisely added to the solution in the flask, andallowed to react for 3 hours at −10° C. When the reaction was completed,water was slowly added until reactivity was undetecable. An organiclayer was extracted with water and ethyl acetate, water was removed withmagnesium sulfate, and concentrated at a low pressure. The resultant wasthen purified by using column chromatography by using hexane and ethylacetate as an eluent to obtain 47 g of Compound 33-2 (234.08 mmol)(yield: 76%).

Synthesis of Compound 33-3

40 g of Compound 33-2 (199 mmol), 48.6 g of iodobenzene (238 mmol), 0.89g of tris(dibenzylideneacetone)dipalladium(0) (4 mmol), 2.47 g of2,2-bisdiphenylphosphino-1,1′-binaphthyl (4 mmol), and 38.19 g of sodiumtert-butoxide (397 mmol) were added to 400 ml of toluene in a 1 L roundbottom flask, and the solution was refluxed for 8 hours. Aftercompleting the reaction, the solution was filtered through Celite,concentrated at a low pressure, and purified by using columnchromatography by using hexane as an eluent to obtain 44 g of Compound33-3 (157.21 mmol) (yield: 79%).

Synthesis of Compound 33-4

44 g of Compound 33-3 (158 mmol) and 130 ml of dimethylformamide wereadded to a 500 ml round bottom flask, and a temperature of the solutionwas decreased to 0° C. 25.2 g of N-bromosuccinimide (142 mmol) wasdissolved in 220 ml of dimethylformamide and slowly and dropwisely addedto the solution. When the addition was completed, a temperature of thesolution was increased to ambient temperature, and then the solution wasstirred for 2 hours. When the reaction was completed, an organic layerwas extracted with water and dichloromethane, water was removed withmagnesium sulfate, and concentrated at a low pressure. Hexane was addedto the produced crystals, and the solution was filtered to obtain 45 gof Compound 33-4 (126.4 mmol) (yield: 80%).

Synthesis of Compound 33-5

40 g of Compound 33-4 (112 mmol), 34 g of bis(pinacolato)diboron (134mmol), 2.73 g of palladium(II)chloride-1-1′-bis(diphenylphosphino)ferrocene (3 mmol), 32.9 g ofpotassium acetate (335 mmol), and 480 ml of toluene were added to a 1 Lround bottom flask, and the solution was refluxed for 8 hours. Aftercompleting the reaction, the solution was filtered through Celite,concentrated at a low pressure, and purified by using columnchromatography by using hexane and ethyl acetate as an eluent to obtain26 g of Compound 33-5 (64.96 mmol) (yield: 58%).

Synthesis of Compound 33

5.0 g of Compound 23-8 (13.44 mmol), 6.50 g of Compound 33-5 (16.13mmol), 0.27 g of tetrakis(triphenylphosphine) palladium (0.20 mmol),2.79 g of potassium carbonate (20.16 mmol), 25 ml of 1,4-dioxane, 25 mlof toluene, and 10 ml of water were added to a round bottom flask, andthe solution was refluxed. When the reaction was completed, water andhexane was added thereto. The produced crystals were filtered. Thecrystals were re-crystallized to obtain 5.51 g of Compound 33 (9.68mmol) (yield: 72%).

MS: m/z 569[M]+

Synthesis Example 4: Compound 35

5.60 g of Compound 35 (8.74 mmol) (yield: 65%) was obtained in the samemanner as in the synthesis of Compound 33 of Synthesis Example 3, exceptthat (4-iodophenyl)trimethylsilane was used instead of iodobenzene.

MS: m/z 641 [M]+

Synthesis Example 5: Compound 37

5.31 g of Compound 37 (8.33 mmol) (yield: 62%) was obtained in the samemanner as in the synthesis of Compound 33 of Synthesis Example 3, exceptthat trimethyl(4-(trifluoromethyl)phenyl)silane was used instead ofiodobenzene.

MS: m/z 637 [M]+

Example 1

An ITO glass substrate (available from Corning Co.) including an ITOlayer having a thickness of 15 Ω/cm² (1,200 Å), as a substrate and ananode, was cut to a size of 50 mm×50 mm×0.7 mm, washed with ultrasonicwaves in isopropyl alcohol and pure water for 5 minutes each, and thencleaned with UV and ozone for 30 minutes. The ITO glass substrate wasthen mounted on a vacuum depositor.

4,4′,4″-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (2T-NATA) wasdeposited on the ITO anode to form an HIL having a thickness of 600 Å,and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was depositedon the HIL to form an HTL having a thickness of 300 Å.

β-ADN (a host) and Compound 23 (a dopant) were co-deposited at a weightratio of 95:5 on the HTL to form an EML having a thickness of 400 Å.

Then, Compound 201 was deposited on the EML to form an ETL having athickness of 300 Å. LiF was deposited on the ETL to form an EIL having athickness of 10 Å, and Al was deposited on the EIL to form a secondelectrode (a cathode) having a thickness of 1,100 Å, thereby completingmanufacture of an OLED. An apparatus for deposition in the specificationwas Suicel plus 200 depositor available from Sunic System.

Example 2

An OLED was manufactured in the same manner as in Example 1, except thatCompound 25 was used instead of Compound 23 in the formation of the EML.

Example 3

An OLED was manufactured in the same manner as in Example 1, except thatCompound 33 was used instead of Compound 23 in the formation of the EML.

Example 4

An OLED was manufactured in the same manner as in Example 1, except thatCompound 35 was used instead of Compound 23 in the formation of the EML.

Example 5

An OLED was manufactured in the same manner as in Example 1, except thatCompound 37 was used instead of Compound 23 in the formation of the EML.

Comparative Example 1

An OLED was manufactured in the same manner as in Example 1, except thatDopant A was used instead of Compound 23 in the formation of the EML.

Comparative Example 2

An OLED was manufactured in the same manner as in Example 1, except thatDopant B was used instead of Compound 23 in the formation of the EML.

Evaluation

Driving voltages, current densities, efficiencies, and color purities ofthe OLEDs prepared in Examples 1 to 5 and Comparative Examples 1 and 2were evaluated by using Kethley SMU 236 and PR650 Spectroscan SourceMeasurement Unit (PhotoResearch), and the results are shown in Table 1(T95 life was time consumed for an OLED to have 95% reduced brightnessafter driving the device under a condition of a current density of 10mA/cm² compared to its initial brightness). Results are shown in Table1, below.

TABLE 1 Driving Color voltage Efficiency coordination T95 Life HostDopant [V] [cd/A] CIEx CIEy [hr] Example 1 β-ADN Compound 23 3.5 5.50.150 0.118 220 Example 2 β-ADN Compound 25 3.5 5.4 0.150 0.124 200Example 3 β-ADN Compound 33 3.5 5.5 0.149 0.120 240 Example 4 β-ADNCompound 35 3.4 5.6 0.150 0.126 180 Example 5 β-ADN Compound 37 3.2 4.80.148 0.130 160 Comparative β-ADN Dopant A 4.5 4.2 0.152 0.162  70Example 1 Comparative 1 β-ADN Dopant B 4.4 5.4 0.151 0.154 120 Example 2

Referring to Table 1, when an OLED included a compound having astructure represented by Formula 1 as a dopant of a blue emission layer,the OLED exhibited better efficiencies and lifespan than those ofanother OLED including a different compound as the dopant.

By way of summation and review, some blue organic light-emitting devicesincluding an anthracene derivative may have room for improvement interms of its color purity, efficiency, and lifespan. According to anembodiment, an organic light-emitting device may have a high colorpurity, a high efficiency, and a long lifespan by including anon-arylamine compound of a fluorene-based derivative as a blue organiclight-emitting material.

As described above, an OLED including the compound according to the oneor more of the above embodiments may have improved color purity, a highefficiency, and a long lifespan.

Example embodiments have been disclosed herein, and although specificterms are employed, they are used and are to be interpreted in a genericand descriptive sense only and not for purpose of limitation. In someinstances, as would be apparent to one of ordinary skill in the art asof the filing of the present application, features, characteristics,and/or elements described in connection with a particular embodiment maybe used singly or in combination with features, characteristics, and/orelements described in connection with other embodiments unless otherwisespecifically indicated. Accordingly, it will be understood by those ofskill in the art that various changes in form and details may be madewithout departing from the spirit and scope of the present invention asset forth in the following claims.

What is claimed is:
 1. A compound represented by Formula 1, below:

wherein, in Formula 1, L is selected from a single bond, a substitutedor unsubstituted C₃-C₁₀ cycloalkylene group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkylene group, a substituted orunsubstituted C₃-C₁₀ cycloalkenylene group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₂-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group; R₁to R₅ are each independently selected from a hydrogen, a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group,carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and—B(Q₆)(Q₇); Ar₁ is selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇), provided thatAr₁ does not include a —N(Q₁)(Q₂) moiety; a, b, c, and d are eachindependently an integer selected from 0 to 6; at least one substituentselected from the substituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀alkenyl group, substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀alkoxy group, substituted C₃-C₁₀ cycloalkyl group, substituted C₂-C₁₀heterocycloalkyl group, substituted C₃-C₁₀ cycloalkenyl group,substituted C₂-C₁₀ heterocycloalkenyl group, substituted C₆-C₆₀ arylgroup, substituted C₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthiogroup, substituted C₂-C₆₀ heteroaryl group, substituted monovalentnon-aromatic condensed polycyclic group, and substituted monovalentnon-aromatic condensed heteropolycyclic group is selected from: adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, carboxylic acid or a salt thereof, a sulfonic acid or asalt thereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkylgroup, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇); a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group; aC₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic groupand a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, carboxylic acid ora salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid ora salt thereof, C₁-C₆₀ alkyl group, C₂-C₆₀ alkenyl group, C₂-C₆₀ alkynylgroup, C₁-C₆₀ alkoxy group, C₃-C₁₀ cycloalkyl group, C₂-C₁₀heterocycloalkyl group, C₃-C₁₀ cycloalkenyl group, C₂-C₁₀heterocycloalkenyl group, C₆-C₆₀ aryl group, C₆-C₆₀ aryloxy group,C₆-C₆₀ arylthio group, C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇); and —N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);wherein Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ are eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group¹, a hydrazone group, a carboxylic acid or asalt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or asalt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₂-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.
 2. Thecompound as claimed in claim 1, wherein, in Formula 1, R₁ and R₂ areeach independently selected from a substituted or unsubstituted C₁-C₆₀alkyl group and a substituted or unsubstituted C₆-C₆₀ aryl group.
 3. Thecompound as claimed in claim 1, wherein, in Formula 1, R₁ and R₂ areeach independently a methyl group or a phenyl group.
 4. The compound asclaimed in claim 1, wherein, in Formula 1, R₃ to R₅ are eachindependently a hydrogen or a deuterium.
 5. The compound as claimed inclaim 1, wherein, in Formula 1, Ar₁ is selected from a substituted orunsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.6. The compound as claimed in claim 1, wherein, in Formula 1, Ar₁ is agroup represented by one of Formulae 7a to 7f, below:

wherein, in Formulae 7a to 7f, R₃₁ to R₄₄ are each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a substituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₆-C₂₀ aryl group, a substituted or unsubstituted C₁-C₂₀heteroaryl group, a substituted or unsubstituted monovalent non-aromaticcondensed polycyclic group, and a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group; p is aninteger selected from 1 to 4; when p is 2 or greater, each R₃₁ isidentical to or different from each other; and * is a binding site to aneighboring atom.
 7. The compound as claimed in claim 6, wherein, inFormula 1, adjacent ones of the plurality of R₃₁ link to each other andform a ring.
 8. The compound as claimed in claim 1, wherein, in Formula1, a and d are each independently an integer selected from 0 to 4, and asum of a and d is
 4. 9. The compound as claimed in claim 1, wherein, inFormula 1, b is 1 or
 2. 10. The compound as claimed in claim 1, wherein,in Formula 1, c is an integer selected from 0 to
 6. 11. The compound asclaimed in claim 1, wherein the compound represented by Formula 1 isrepresented by Formula 2, below:

wherein, in Formula 2, R₁₀₁ is selected from a hydrogen, a deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a substituted or unsubstituted C₁-C₂₀alkyl group, a substituted or unsubstituted C₆-C₂₀ aryl group, asubstituted or unsubstituted C₁-C₂₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group.
 12. The compound as claimed in claim 1, whereinthe compound represented by Formula 1 is represented by Formula 3,below:

wherein, in Formula 3, Naph denotes a naphthyl group.
 13. The compoundas claimed in claim 12, wherein a

moiety of Formula 3 is or

in which * denotes a binding site to a neighboring atom.
 14. Thecompound as claimed in claim 1, wherein the compound represented byFormula 1 is one of Compounds 1 to 88, below:


15. An organic light-emitting device, comprising: a first electrode; asecond electrode facing the first electrode; and an organic layer thatbetween the first electrode and the second electrode, the organic layerincluding an emission layer, wherein the organic layer includes thecompound as claimed in claim
 1. 16. The organic light-emitting device asclaimed in claim 15, wherein the organic layer is formed by using a wetprocess.
 17. The organic light-emitting device as claimed in claim 15,wherein: the first electrode is an anode, the second electrode is acathode, and the organic layer includes: a hole transport region betweenthe first electrode and the emission layer, the hole transport regionincluding at least of a hole injection layer, a hole transport layer, abuffer layer, and an electron blocking layer, and an electron transportregion between the emission layer and the second electrode, the electrontransport region including at least one of a hole blocking layer, anelectron transport layer, and an electron injection layer.
 18. Theorganic light-emitting device as claimed in claim 17, wherein theemission layer includes the compound.
 19. The organic light-emittingdevice as claimed in claim 17, wherein the electron transport regionincludes a metal complex.
 20. A flat display apparatus, comprising: athin film transistor, the thin film transistor including a sourceelectrode and a drain electrode; and the organic light-emitting deviceas claimed in claim 15, wherein the first electrode of the organiclight-emitting device is electrically connected with the sourceelectrode or the drain electrode of the thin film transistor.
 21. Acompound represented by Formula 1, below:

wherein, in Formula 1, L is selected from a single bond, a substitutedor unsubstituted C₃-C₁₀ cycloalkylene group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkylene group, a substituted orunsubstituted C₃-C₁₀ cycloalkenylene group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₂-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group; R₁to R₅ are each independently selected from a hydrogen, a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group,carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and—B(Q₆)(Q₇); a, b, c, and d are each independently an integer selectedfrom 0 to 6; at least one substituent selected from the substitutedC₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀alkynyl group, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀cycloalkyl group, substituted C₂-C₁₀ heterocycloalkyl group, substitutedC₃-C₁₀ cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₂-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic condensed heteropolycyclic group isselected from: a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, carboxylic acid or a salt thereof, a sulfonicacid or a salt thereof, a phosphoric acid or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted withat least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇); a C₃-C₁₀ cycloalkylgroup, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group; a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group and a monovalent non-aromaticcondensed heteropolycyclic group, each substituted with at least oneselected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, carboxylic acid or a salt thereof, a sulfonicacid or a salt thereof, a phosphoric acid or a salt thereof, C₁-C₆₀alkyl group, C₂-C₆₀ alkenyl group, C₂-C₆₀ alkynyl group, C₁-C₆₀ alkoxygroup, C₃-C₁₀ cycloalkyl group, C₂-C₁₀ heterocycloalkyl group, C₃-C₁₀cycloalkenyl group, C₂-C₁₀ heterocycloalkenyl group, C₆-C₆₀ aryl group,C₆-C₆₀ aryloxy group, C₆-C₆₀ arylthio group, C₂-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇); and —N(Q₃₁)(Q₃₂),—Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇); wherein Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁to Q₂₇, and Q₃₁ to Q₃₇ are each independently selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensedpolycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group, and wherein Ar_(t) is a group represented by oneof Formulae 7a to 7f, below:

wherein, in Formulae 7a to 7f, R₃₁ to R₄₄ are each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a substituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₆-C₂₀ aryl group, a substituted or unsubstituted C₁-C₂₀heteroaryl group, a substituted or unsubstituted monovalent non-aromaticcondensed polycyclic group, and a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group; p is aninteger selected from 1 to 4; when p is 2 or greater, each R₃₁ isidentical to or different from each other; and * is a binding site to aneighboring atom.